Ethyl bromoacetate → Ethyl 2-(3-fluorophenoxy)acetate

Temperature

0 °C

A 50 ml three-necked round-bottomed flask equipped with temperature probe and nitrogen bubbler was charged with Sodium Hydride (785 mg, 19.6 mmol) and DMF (10.0 ml) and cooled to 0° C. A solution of 3-Fluorophenol (2.00 g, 17.8 mmol) in DMF (2.0 ml) was added dropwise maintaining reaction temperature below 10° C. The mixture was stirred for an additional 15 minutes then Ethyl bromoacetate (2.48 ml, 22.3 mmol) was added dropwise maintaining the reaction temperature below 10° C. The reaction was stirred at room temperature for 4 hours. The reaction was then concentrated under reduced pressure and the crude product was taken up in Ethyl acetate, washed with water, dried (Na2SO4), filtered, concentrated and further purified via flash chromatography using 4:1/heptane:Ethyl acetate as eluant. Fractions containing product were combined and concentrated to afford (3-Fluoro-phenoxy)-acetic acid ethyl ester (2.26 g, 69%) as a clear oil.

1. customA 50 ml three-necked round-bottomed flask equipped with temperature probe and nitrogen bubbler
2. temperaturemaintaining
3. customreaction temperature below 10° C
4. temperaturemaintaining the reaction temperature below 10° C
5. stirringThe reaction was stirred at room temperature for 4 hours
6. concentrationThe reaction was then concentrated under reduced pressure
7. washwashed with water
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customfurther purified via flash chromatography
12. additionFractions containing product
13. concentrationconcentrated

ORD record

ord-49f0e5c2b467485584917e41eab1e5aa

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217027B2